Crystal structure of 1-(4-methyl-phen-yl)-3-(propan-2-yl-idene-amino)-thio-urea

Mukesh M Jotani; Chien Ing Yeo; Edward R T Tiekink

doi:10.1107/S2056989015017624

Crystal structure of 1-(4-methyl-phen-yl)-3-(propan-2-yl-idene-amino)-thio-urea

Acta Crystallogr E Crystallogr Commun. 2015 Sep 26;71(Pt 10):1236-41. doi: 10.1107/S2056989015017624. eCollection 2015 Oct 1.

Authors

Mukesh M Jotani¹, Chien Ing Yeo², Edward R T Tiekink³

Affiliations

¹ Department of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad, Gujarat 380001, India.
² Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia.
³ Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia ; Centre for Chemical Crystallography, Faculty of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia.

Abstract

In the title thio-semicarbazone, C11H15N3S, the p-tolyl-N-H and imino-N-H groups are anti and syn, respectively, to the central thione-S atom. This allows for the formation of an intra-molecular p-tolyl-N-H⋯N(imino) hydrogen bond. The mol-ecule is twisted with the dihedral angle between the p-tolyl ring and the non-hydrogen atoms of the N=CMe2 residue being 29.27 (8)°. The crystal packing features supra-molecular layers lying in the bc plane whereby centrosymmetric aggregates sustained by eight-membered thio-amide {⋯HNCS}2 synthons are linked by further N-H⋯S hydrogen bonds. Layers are connected via methyl-C-H⋯π inter-actions. The supra-molecular aggregation was further investigated by an analysis of the Hirshfeld surface and comparison made to related structures.

Keywords: Hirshfeld surface analysis; crystal structure; hydrogen bonding; thiosemicarbazone; thiourea derivative.